1,2-Dichloroethane → 4-(5-bromo-2-chloropyrimidin-4-yl)-N-(6-chloro-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide

HRID 2169567Notes

Reaction equation

HRID 2169567 reaction equation
[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([OH:17])=O)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[Cl:33][C:34]1[CH:42]=[C:41]2[C:37]([CH2:38][CH2:39][CH:40]2[NH2:43])=[CH:36][CH:35]=1.C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([NH:43][CH:40]2[C:41]3[C:37](=[CH:36][CH:35]=[C:34]([Cl:33])[CH:42]=3)[CH2:38][CH2:39]2)=[O:17])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 529877246-chloro-2,3-dihydro-1H-inden-1-amine hydrochlorideHCID 86670107HCID 86670107, compound

Product 1

HCID 866701154-(5-bromo-2-chloropyrimidin-4-yl)-N-(6-chloro-2,3-dihydro-1H-inden-1-yl)morpholine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x31 using 4-(5-bromo-2-chloropyrimidin-4-yl)morpholine-3-carboxylic acid (PREPARATION x30, 750 mg, 2.325 mmol), EDC (669 mg, 3.49 mmol), HOBt (534 mg, 3.49 mmol), 6-chloro-2,3-dihydro-1H-inden-1-amine hydrochloride (712 mg, 3.49 mmol), and triethylamine (0.486 mL, 3.49 mmol) in DMF (15 mL). 1H NMR (400 MHz, DMSO-d6) δ 1.78-1.95 (m, 1 H), 2.36-2.47 (m, 1 H), 2.70-2.96 (m, 2 H), 3.48-3.80 (m, 3 H), 3.86-3.98 (m, 1 H), 4.21-4.44 (m, 2 H), 4.77-4.93 (m, 1 H), 5.28-5.43 (m, 1 H), 7.27 (s, 3 H), 8.47 (d, J=7.58 Hz, 2 H). ESI-MS m/z [M+H]+ calc'd for C18H17Br2Cl2N4O2, 470.99; found 471.3.

Sources & evidence

ORD record
ord-d45426af40e5489697bc89259cb64afd
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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